alpha-naphthacetyl-amino acids and process for the manufacture of same



Patented Nov. 14, 1939 UNITED STATES PATENT OFFICE a NAPHTHACETYL AMINO ACIDS AND PROCESS SAME FOR THE MANUFACTURE Otto Isler, Basel, Switzerland, assignor to Hoffman-La Roche Inc., Nutley, N. J., a corporation of New Jersey No Drawing. Application January 13, 1939, .Se-

rial No. 250,845. In 1938 12 Claims.

It has been found that the salts of a-naphthacetyl-amino acids under suitable conditions stimulate the striking of roots from cuttings, the

Example 1 113 parts by weight of u-naphthyl-acetyl chloride, prepared from 100 parts by weight of anaphthyl-acetic acid by means of thionyl chloride, are added dropwise to a solution of 50 parts by weight of glycocoll in 500 parts by weight of 20' 3-n soda solution while stirring. The clear solution is diluted with 1000 parts by weight of water and then acidified by the addition of 3-n hydrochloric acid. Thereby, the anaphthacetyl gly cine separates as a voluminous white precipitate which is sucked off, dried, digested twice with 2000 parts by weight of ether and then recrystallised from 25 parts by weight of 30% alcohol. The xnaphthacetyl glycine melts at 153-154" C. It forms alkali salts easily soluble in Water.

Example 2 42 parts by weight of a-naphthyl-acetyl chloride are added dropwise to an alkaline solution of 28 parts by weight of l-leucin in the course of one 3 hour while stirring vigorously. After three hours the product is acidified, the condensation product sucked off, again dissolved in a solution of caustic soda and precipitated once more with hydrochloric acid. The precipitate is then sucked off,

dried and twice recrystallised from. benzene. The

a-naphthacetyl-l-leucin melts at 146-147 C. It forms alkali salts easily soluble in water.

Example 3 6 parts by weight of a-naphthylacety1 chlo- Switzerland February 2,

1. Compounds of the general formula l RCH.C OOH wherein R and R are selected from the group comprising hydrogen and alkyl radicals. 2. u-Naphthacetyl glycine.

3. a-Naphthacetyl leucin.

4. a-Naphthacetyl sarcosine.

5. Process for the manufacture of a-naphthacetyl-amino acids of the general formula wherein R and R, represent an aliphatic alkyl or hydrogen, comprising reacting an a-naphthylacetic acid halide with amino acids.

' 6. Process for the manufacture of a-naphthacetyl-amino acids of the general formula wherein R and R. represent an aliphatic alkyl or hydrogen, comprising reacting an a-naphthylacetic acid halide with amino acids in alkaline solution.

'7. Process for the manufacture of a-n'aphthacetyl glycine comprising the reaction of a-naphthyl-acetic acid chloride with glycocoll.

8. Process for the manufacture of a-naphthacetyl glycine comprising the reaction of a-naphthyl-acetic acid chloride with glycocoll in alkaline solution.

9. Process for the manufacture of OL'DEIJhth" acetyl-l-leucin comprising the reaction of ornaphthyl-acetic acid chloride with l-leucin.

10. Process for the manufacture of ill-naphthacetyl-l-leucin comprising the reaction of a naphthyl-acetic acid chloride with l-leucin in alkaline solution.

11. Process for the manufacture of iii-naphthacetyl sarcosine comprising the reaction of o:- naphthyl-acetic acid chloride with sarcosine.

12. Process for the manufacture of a-naphthacetyl sarcosine comprising the reaction of 0cnaphthyl-acetic acid chloride with sarcosine in alkaline solution.

OTTO ISLER. 

